Chicago Favorites Ultimate Food and Walking Tour with Deep-Dish Pizza, Hot Dog, and Italian Beef
by Bobby's Bike, Hike & Food Tours - Chicago
Choose from 2 available options
How do you want to book?
✓Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.
Book on Viator Confirmed right away, but you pay full price.$169.98Overview
This three-hour walking tour in downtown Chicago visits the city’s favorite foods and key landmarks. The tour covers about 1.25 miles at a comfortable pace, with some walking above ground and some through the Chicago Pedway tunnels depending on weather. It begins at a designated meeting point that varies by start time. Morning tours start between 11am and 12pm and begin with a slice of deep-dish pizza served immediately. Stops include Millennium Park with Cloud Gate (The Bean) and Crown Fountain, the Chicago Theatre, the Magnificent Mile, and the Wrigley Building. The original Chicago brownie is served on morning tours as dessert. Evening tours start at 5:30pm from Gino’s East with deep-dish pizza served first, followed by a visit to a local hot dog stand on Michigan Avenue to taste a full Chicago-style hot dog with mustard, relish, onions, tomato wedges, a pickle spear, sport peppers, and celery salt. The tour continues to the Palmer House Hilton historic lobby for a sample of the Italian beef sandwich, which is slow-roasted beef on Italian bread served with au jus and either giardiniera or sweet peppers. Evening tours include gelato instead of the brownie. Along the route, the guide shares information about Chicago’s food culture, architecture, and local history while offering tips on attractions and activities. Each ticket includes a free two-hour bike or kayak rental valid within three days of the tour, weather permitting. Bike rentals are available year-round except on Thanksgiving and Christmas at Bobby’s Bike Hike World Headquarters near Lake Shore Drive. Kayak rentals operate mid-May to mid-October at Ohio Street Beach on Lake Michigan, excluding certain holiday weekends. Gratuities, hotel transfers, and alcoholic drinks are not included.
Highlights
What's included
What's not included
Itinerary
Daytime Tour Starting Point
The daytime Chicago Food Tours at 11am, 11:30am, and 12pm begin at a designated meeting spot where participants meet their guide who shares Chicago’s history and local stories. Before visiting The Bean for photos, guests enjoy a hot, cheesy deep-dish pizza with the signature stuffed crust. This stop serves as the initial food experience on the tour.
20 min
Evening Tour Starting Point
The 5:30pm evening tour starts at Gino’s East, where the guide introduces Chicago’s history and shares lively stories. Guests then taste a golden, cheesy deep-dish pizza that has been popular since the 1960s. This marks the first food stop on the evening tour.
20 min
Wrigley Building
Guests try an authentic Chicago-style hot dog made with an all-beef frankfurter in a poppy seed bun, topped with yellow mustard, neon green relish, onions, tomato wedges, a dill pickle spear, sport peppers, and celery salt. Ketchup is not included. The hot dog is served at a local stand such as Relish on Michigan Avenue. The hot dog partner may vary to keep the experience fresh.
20 min
Palmer House Hilton Historic Lobby
The tour includes a stop to taste Chicago’s Italian Beef sandwich, featuring thinly sliced, slow-roasted beef on fresh Italian bread, dipped in herb-infused au jus, and topped with spicy giardiniera or sweet peppers. The location rotates among iconic local spots, offering different versions on different days.
20 min
The Magnificent Mile
Available only on AM tours, this stop features the original recipe brownie created in 1893 at the Palmer House Hotel for the Chicago World’s Fair. The brownie is rich and fudgy, topped with apricot glaze and walnuts, representing the first brownie ever made.
10 min
The Chicago Theatre
Guests sample Garrett’s famous Chicago Mix popcorn, a combination of buttery caramel corn and cheddar popcorn. This sweet-and-salty snack is served without waiting in lines, offering a popular local treat.
10 min
Millennium Park Walk
On AM tours only, participants walk through Millennium Park, a public space built over a parking garage and rail yard. The guide shares stories about landmarks like Cloud Gate, Crown Fountain, and Jay Pritzker Pavilion while guests enjoy deep-dish pizza and Garrett’s popcorn.
15 min
Millennium Park
Also on AM tours only, the group visits Chicago’s Cloud Gate, known as The Bean, a stainless steel sculpture reflecting the city skyline. The guide explains its history while guests enjoy local food items such as deep-dish pizza and hot dogs.
10 min
Cloud Gate
The tour passes by the Chicago Theatre, noted for its French Baroque architecture and the large “CHICAGO” sign added in the 1980s. The guide shares stories about the theatre’s history and famous performers as guests continue to enjoy Chicago’s signature foods.
10 min
Crown Fountain
Guests walk along Michigan Avenue’s Magnificent Mile, viewing historic landmarks including the Tribune Tower, Wrigley Building, and the start of Route 66. The walk is combined with tasting deep-dish pizza, Italian beef, and other local dishes.
15 min
Jay Pritzker Pavilion
On PM tours only, the group passes the Chicago Historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871. The guide discusses its history while guests enjoy bites of hot dogs, Italian beef, and deep-dish pizza.
5 min
Crown Fountain Visit
On AM tours only, the group visits Crown Fountain in Millennium Park, featuring two glass block towers projecting faces of Chicago residents that change expressions and spray water in summer. The guide shares the story behind the art while guests enjoy deep-dish pizza and local snacks.
10 min
Wrigley Building View
Guests view the Wrigley Building along the Chicago River, known for its white terra cotta exterior and clock tower. It was the city’s first air-conditioned office building. The stop combines architectural appreciation with tasting Chicago’s famous foods.
5 min
Historic Water Tower
On PM tours only, the group passes the Holy Name Cathedral, a Gothic Revival church rebuilt after the Great Chicago Fire. Outside, a bronze cross marks where a mobster was killed during Chicago’s gangster era. The guide shares these stories while guests enjoy Italian beef, hot dogs, and deep-dish pizza.
5 min
Holy Name Cathedral
On AM tours only, the tour passes the Jay Pritzker Pavilion in Millennium Park, a steel concert venue designed by Frank Gehry with a trellis that carries sound evenly. The stop is paired with bites like deep-dish pizza and Garrett’s popcorn.
5 min
The Loop
Guests explore the Chicago Loop, surrounded by elevated train tracks and home to theaters, skyscrapers, and landmarks like the Art Institute and Riverwalk. The tour combines walking with tasting deep-dish pizza and the original brownie.
Chicago Pedway
Depending on the season, the tour goes through the Pedway, an underground network of tunnels and bridges beneath downtown, or above ground along the Loop’s promenades. The route covers 1.25 miles over 3 hours with multiple food stops and city views.
Bike or Kayak Rental Info
Tour participants receive a free 2-hour bike or kayak rental to be used within plus or minus 3 days of booking. Bike rentals take place year-round at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL 60611. Renters can explore the 20-mile Lakefront Bike Trail. Kayak rentals occur at Bobby’s Kayak, 550 E. Grand Avenue, Ohio Street Beach, from mid-May to mid-October, weather permitting. Kayaking is only available June through September on Lake Michigan and excludes Saturdays between Memorial Day weekend and Labor Day. No discounts apply if the activity is not used or weather restricts participation.
Meeting point
EVENING TOURS (5:30pm) For your evening Chicago Food tour, your Guide will be in front of the restaurant, wearing a Bobby's Bike Hike shirt with branded paddle. Then you will begin your Food tour in Chicago.
End point
EVENING TOURS (5:30pm): This is where your Chicago Food Tour will end.
Languages
Cancellation policy
- Cancel at least 24 hours before start for a full refund.
Additional info
Chicago Favorites Ultimate Food and Walking Tour with Deep-Dish Pizza, Hot Dog, and Italian Beef
by Bobby's Bike, Hike & Food Tours - Chicago
Choose from 2 available options
How do you want to book?
✓Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.
Book on Viator Confirmed right away, but you pay full price.$169.98Overview
This three-hour walking tour in downtown Chicago visits the city’s favorite foods and key landmarks. The tour covers about 1.25 miles at a comfortable pace, with some walking above ground and some through the Chicago Pedway tunnels depending on weather. It begins at a designated meeting point that varies by start time. Morning tours start between 11am and 12pm and begin with a slice of deep-dish pizza served immediately. Stops include Millennium Park with Cloud Gate (The Bean) and Crown Fountain, the Chicago Theatre, the Magnificent Mile, and the Wrigley Building. The original Chicago brownie is served on morning tours as dessert. Evening tours start at 5:30pm from Gino’s East with deep-dish pizza served first, followed by a visit to a local hot dog stand on Michigan Avenue to taste a full Chicago-style hot dog with mustard, relish, onions, tomato wedges, a pickle spear, sport peppers, and celery salt. The tour continues to the Palmer House Hilton historic lobby for a sample of the Italian beef sandwich, which is slow-roasted beef on Italian bread served with au jus and either giardiniera or sweet peppers. Evening tours include gelato instead of the brownie. Along the route, the guide shares information about Chicago’s food culture, architecture, and local history while offering tips on attractions and activities. Each ticket includes a free two-hour bike or kayak rental valid within three days of the tour, weather permitting. Bike rentals are available year-round except on Thanksgiving and Christmas at Bobby’s Bike Hike World Headquarters near Lake Shore Drive. Kayak rentals operate mid-May to mid-October at Ohio Street Beach on Lake Michigan, excluding certain holiday weekends. Gratuities, hotel transfers, and alcoholic drinks are not included.
Highlights
What's included
What's not included
Itinerary
Daytime Tour Starting Point
The daytime Chicago Food Tours at 11am, 11:30am, and 12pm begin at a designated meeting spot where participants meet their guide who shares Chicago’s history and local stories. Before visiting The Bean for photos, guests enjoy a hot, cheesy deep-dish pizza with the signature stuffed crust. This stop serves as the initial food experience on the tour.
20 min
Evening Tour Starting Point
The 5:30pm evening tour starts at Gino’s East, where the guide introduces Chicago’s history and shares lively stories. Guests then taste a golden, cheesy deep-dish pizza that has been popular since the 1960s. This marks the first food stop on the evening tour.
20 min
Wrigley Building
Guests try an authentic Chicago-style hot dog made with an all-beef frankfurter in a poppy seed bun, topped with yellow mustard, neon green relish, onions, tomato wedges, a dill pickle spear, sport peppers, and celery salt. Ketchup is not included. The hot dog is served at a local stand such as Relish on Michigan Avenue. The hot dog partner may vary to keep the experience fresh.
20 min
Palmer House Hilton Historic Lobby
The tour includes a stop to taste Chicago’s Italian Beef sandwich, featuring thinly sliced, slow-roasted beef on fresh Italian bread, dipped in herb-infused au jus, and topped with spicy giardiniera or sweet peppers. The location rotates among iconic local spots, offering different versions on different days.
20 min
The Magnificent Mile
Available only on AM tours, this stop features the original recipe brownie created in 1893 at the Palmer House Hotel for the Chicago World’s Fair. The brownie is rich and fudgy, topped with apricot glaze and walnuts, representing the first brownie ever made.
10 min
The Chicago Theatre
Guests sample Garrett’s famous Chicago Mix popcorn, a combination of buttery caramel corn and cheddar popcorn. This sweet-and-salty snack is served without waiting in lines, offering a popular local treat.
10 min
Millennium Park Walk
On AM tours only, participants walk through Millennium Park, a public space built over a parking garage and rail yard. The guide shares stories about landmarks like Cloud Gate, Crown Fountain, and Jay Pritzker Pavilion while guests enjoy deep-dish pizza and Garrett’s popcorn.
15 min
Millennium Park
Also on AM tours only, the group visits Chicago’s Cloud Gate, known as The Bean, a stainless steel sculpture reflecting the city skyline. The guide explains its history while guests enjoy local food items such as deep-dish pizza and hot dogs.
10 min
Cloud Gate
The tour passes by the Chicago Theatre, noted for its French Baroque architecture and the large “CHICAGO” sign added in the 1980s. The guide shares stories about the theatre’s history and famous performers as guests continue to enjoy Chicago’s signature foods.
10 min
Crown Fountain
Guests walk along Michigan Avenue’s Magnificent Mile, viewing historic landmarks including the Tribune Tower, Wrigley Building, and the start of Route 66. The walk is combined with tasting deep-dish pizza, Italian beef, and other local dishes.
15 min
Jay Pritzker Pavilion
On PM tours only, the group passes the Chicago Historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871. The guide discusses its history while guests enjoy bites of hot dogs, Italian beef, and deep-dish pizza.
5 min
Crown Fountain Visit
On AM tours only, the group visits Crown Fountain in Millennium Park, featuring two glass block towers projecting faces of Chicago residents that change expressions and spray water in summer. The guide shares the story behind the art while guests enjoy deep-dish pizza and local snacks.
10 min
Wrigley Building View
Guests view the Wrigley Building along the Chicago River, known for its white terra cotta exterior and clock tower. It was the city’s first air-conditioned office building. The stop combines architectural appreciation with tasting Chicago’s famous foods.
5 min
Historic Water Tower
On PM tours only, the group passes the Holy Name Cathedral, a Gothic Revival church rebuilt after the Great Chicago Fire. Outside, a bronze cross marks where a mobster was killed during Chicago’s gangster era. The guide shares these stories while guests enjoy Italian beef, hot dogs, and deep-dish pizza.
5 min
Holy Name Cathedral
On AM tours only, the tour passes the Jay Pritzker Pavilion in Millennium Park, a steel concert venue designed by Frank Gehry with a trellis that carries sound evenly. The stop is paired with bites like deep-dish pizza and Garrett’s popcorn.
5 min
The Loop
Guests explore the Chicago Loop, surrounded by elevated train tracks and home to theaters, skyscrapers, and landmarks like the Art Institute and Riverwalk. The tour combines walking with tasting deep-dish pizza and the original brownie.
Chicago Pedway
Depending on the season, the tour goes through the Pedway, an underground network of tunnels and bridges beneath downtown, or above ground along the Loop’s promenades. The route covers 1.25 miles over 3 hours with multiple food stops and city views.
Bike or Kayak Rental Info
Tour participants receive a free 2-hour bike or kayak rental to be used within plus or minus 3 days of booking. Bike rentals take place year-round at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL 60611. Renters can explore the 20-mile Lakefront Bike Trail. Kayak rentals occur at Bobby’s Kayak, 550 E. Grand Avenue, Ohio Street Beach, from mid-May to mid-October, weather permitting. Kayaking is only available June through September on Lake Michigan and excludes Saturdays between Memorial Day weekend and Labor Day. No discounts apply if the activity is not used or weather restricts participation.
Meeting point
EVENING TOURS (5:30pm) For your evening Chicago Food tour, your Guide will be in front of the restaurant, wearing a Bobby's Bike Hike shirt with branded paddle. Then you will begin your Food tour in Chicago.
End point
EVENING TOURS (5:30pm): This is where your Chicago Food Tour will end.
Languages
Cancellation policy
- Cancel at least 24 hours before start for a full refund.